His first film was Stonebridge Park (1981) followed by Norwood (1983), The End (1986), Valtos (1987) and The Clouds (1989). These films are typified by their use of subjective camera and voice-over, a technique that was further refined in his longer films London (1994) and Robinson in Space (1997).

Both London and Robinson in Space are narrated by an unnamed character (voiced by Paul Scofield) who accompanies his friend and onetime lover, the unseen Robinson, in a series of excursions around London. Robinson is involved with research into the problems of London and, in the later film, England. The films are seen as a critique of the United Kingdom's economic landscape under the Conservative governments of 1979-97.

In 2000, Keiller completed The Dilapidated Dwelling. This film was made for television, but was never broadcast. It features the voice of Tilda Swinton, and its subject matter is the state of the UK's housing.

Keiller's film Robinson in Ruins was released in November 2010. It was one of the outcomes of a three-year research project entitled The Future of Landscape and the Moving Image and reprised the Robinson character from London and Robinson in Space.[1] The actress Vanessa Redgrave assumed the role of narrator.[2]